data_cu_20170905_4_aza_4helicene_0m_a
_audit_creation_date              2018-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2014/7'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C17 H11 N'
_chemical_formula_sum             'C17 H11 N'
_chemical_formula_weight          229.27
_chemical_absolute_configuration  ?
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'

_cell_length_a                    9.6945(17)
_cell_length_b                    22.594(7)
_cell_length_c                    5.1731(15)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1133.1(5)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     8736
_cell_measurement_temperature     293(2)
_cell_measurement_theta_max       78.45
_cell_measurement_theta_min       3.91
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.603
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             ?
_exptl_crystal_density_diffrn     1.344
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'block'
_exptl_crystal_F_000              480
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.2
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0557
_diffrn_reflns_av_unetI/netI      0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        28
_diffrn_reflns_limit_k_min        -28
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_limit_l_min        -5
_diffrn_reflns_number             17664
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          78.785
_diffrn_reflns_theta_min          3.913
_diffrn_ambient_temperature       293(2)
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        ?
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54178
_diffrn_source                    ?
_reflns_Friedel_coverage          0.656
_reflns_Friedel_fraction_full     0.842
_reflns_Friedel_fraction_max      0.820
_reflns_number_gt                 2077
_reflns_number_total              2245
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        ?
_computing_data_collection        ?
_computing_data_reduction         ?
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution     ?
_refine_diff_density_max          0.150
_refine_diff_density_min          -0.187
_refine_diff_density_rms          0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.0(5)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    0.896
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      163
_refine_ls_number_reflns          2245
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0405
_refine_ls_R_factor_gt            0.0360
_refine_ls_restrained_S_all       0.895
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1031
_refine_ls_wR_factor_ref          0.1088
_refine_special_details           ?
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.042) H7(0.03) H5(0.036) H2(0.037) H3(0.039) H11(0.034)
 H10(0.037) H4(0.038) H9(0.037) H8(0.036) H6(0.037)
 Fixed X: H1(0.0653) H7(0.528) H5(0.7536) H2(0.8181) H3(0.2733) H11(0.3802)
 H10(-0.0595) H4(0.0238) H9(0.2035) H8(0.4197) H6(0.6553)
 Fixed Y: H1(0.7412) H7(0.6659) H5(0.6637) H2(0.6141) H3(0.7743) H11(0.7217)
 H10(0.5851) H4(0.5342) H9(0.5122) H8(0.5254) H6(0.562)
 Fixed Z: H1(1.1312) H7(0.6452) H5(0.5144) H2(0.1403) H3(0.9671) H11(0.6412)
 H10(0.6722) H4(0.3268) H9(0.0166) H8(-0.1448) H6(-0.0881)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 N1 N 0.04007(17) 0.67388(8) 0.9035(4) 0.0319(4) Uani 1 1 d . . . . .
 C1 C 0.1057(2) 0.72038(9) 0.9959(5) 0.0346(5) Uani 1 1 d . . . . .
 H1 H 0.0653 0.7412 1.1312 0.042 Uiso 1 1 calc R U . . .
 C2 C 0.10396(18) 0.64185(8) 0.7149(4) 0.0257(4) Uani 1 1 d . . . . .
 C3 C 0.23881(19) 0.65473(8) 0.6183(4) 0.0235(4) Uani 1 1 d . . . . .
 C4 C 0.30101(19) 0.61564(7) 0.4275(4) 0.0222(4) Uani 1 1 d . . . . .
 C5 C 0.44602(19) 0.61674(8) 0.3531(4) 0.0230(4) Uani 1 1 d . . . . .
 C6 C 0.55119(19) 0.64549(8) 0.4952(4) 0.0252(4) Uani 1 1 d . . . . .
 H7 H 0.5280 0.6659 0.6452 0.030 Uiso 1 1 calc R U . . .
 C7 C 0.6872(2) 0.64405(9) 0.4172(5) 0.0301(5) Uani 1 1 d . . . . .
 H5 H 0.7536 0.6637 0.5144 0.036 Uiso 1 1 calc R U . . .
 C8 C 0.7267(2) 0.61361(8) 0.1950(5) 0.0312(5) Uani 1 1 d . . . . .
 H2 H 0.8181 0.6141 0.1403 0.037 Uiso 1 1 calc R U . . .
 C9 C 0.2330(2) 0.74007(9) 0.9015(5) 0.0322(5) Uani 1 1 d . . . . .
 H3 H 0.2733 0.7743 0.9671 0.039 Uiso 1 1 calc R U . . .
 C10 C 0.2975(2) 0.70816(8) 0.7105(5) 0.0284(4) Uani 1 1 d . . . . .
 H11 H 0.3802 0.7217 0.6412 0.034 Uiso 1 1 calc R U . . .
 C11 C 0.0269(2) 0.59447(9) 0.6054(5) 0.0310(5) Uani 1 1 d . . . . .
 H10 H -0.0595 0.5851 0.6722 0.037 Uiso 1 1 calc R U . . .
 C12 C 0.0784(2) 0.56293(9) 0.4048(5) 0.0318(5) Uani 1 1 d . . . . .
 H4 H 0.0238 0.5342 0.3268 0.038 Uiso 1 1 calc R U . . .
 C13 C 0.21514(19) 0.57304(8) 0.3105(4) 0.0265(4) Uani 1 1 d . . . . .
 C14 C 0.2628(2) 0.53911(8) 0.0952(5) 0.0306(5) Uani 1 1 d . . . . .
 H9 H 0.2035 0.5122 0.0166 0.037 Uiso 1 1 calc R U . . .
 C15 C 0.3927(2) 0.54543(9) 0.0040(4) 0.0296(4) Uani 1 1 d . . . . .
 H8 H 0.4197 0.5254 -0.1448 0.036 Uiso 1 1 calc R U . . .
 C16 C 0.4885(2) 0.58276(8) 0.1358(4) 0.0259(4) Uani 1 1 d . . . . .
 C17 C 0.6290(2) 0.58302(9) 0.0584(4) 0.0306(5) Uani 1 1 d . . . . .
 H6 H 0.6553 0.5620 -0.0881 0.037 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 N1 C1 1.318(3) . ?
 N1 C2 1.363(3) . ?
 C1 H1 0.9300 . ?
 C1 C9 1.399(3) . ?
 C2 C3 1.430(2) . ?
 C2 C11 1.423(3) . ?
 C3 C4 1.455(3) . ?
 C3 C10 1.417(3) . ?
 C4 C5 1.458(2) . ?
 C4 C13 1.409(3) . ?
 C5 C6 1.415(3) . ?
 C5 C16 1.422(3) . ?
 C6 H7 0.9300 . ?
 C6 C7 1.379(3) . ?
 C7 H5 0.9300 . ?
 C7 C8 1.393(3) . ?
 C8 H2 0.9300 . ?
 C8 C17 1.369(3) . ?
 C9 H3 0.9300 . ?
 C9 C10 1.374(3) . ?
 C10 H11 0.9300 . ?
 C11 H10 0.9300 . ?
 C11 C12 1.354(3) . ?
 C12 H4 0.9300 . ?
 C12 C13 1.431(3) . ?
 C13 C14 1.429(3) . ?
 C14 H9 0.9300 . ?
 C14 C15 1.353(3) . ?
 C15 H8 0.9300 . ?
 C15 C16 1.427(3) . ?
 C16 C17 1.420(3) . ?
 C17 H6 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C1 N1 C2 117.60(18) . . ?
 N1 C1 H1 118.2 . . ?
 N1 C1 C9 123.5(2) . . ?
 C9 C1 H1 118.2 . . ?
 N1 C2 C3 123.88(18) . . ?
 N1 C2 C11 116.46(17) . . ?
 C11 C2 C3 119.62(19) . . ?
 C2 C3 C4 119.50(17) . . ?
 C10 C3 C2 115.01(18) . . ?
 C10 C3 C4 125.38(17) . . ?
 C3 C4 C5 124.63(16) . . ?
 C13 C4 C3 117.46(17) . . ?
 C13 C4 C5 117.89(17) . . ?
 C6 C5 C4 124.44(18) . . ?
 C6 C5 C16 116.75(17) . . ?
 C16 C5 C4 118.59(17) . . ?
 C5 C6 H7 119.1 . . ?
 C7 C6 C5 121.7(2) . . ?
 C7 C6 H7 119.1 . . ?
 C6 C7 H5 119.5 . . ?
 C6 C7 C8 121.1(2) . . ?
 C8 C7 H5 119.5 . . ?
 C7 C8 H2 120.5 . . ?
 C17 C8 C7 119.01(19) . . ?
 C17 C8 H2 120.5 . . ?
 C1 C9 H3 120.5 . . ?
 C10 C9 C1 119.0(2) . . ?
 C10 C9 H3 120.5 . . ?
 C3 C10 H11 119.8 . . ?
 C9 C10 C3 120.43(19) . . ?
 C9 C10 H11 119.8 . . ?
 C2 C11 H10 119.8 . . ?
 C12 C11 C2 120.48(19) . . ?
 C12 C11 H10 119.8 . . ?
 C11 C12 H4 119.4 . . ?
 C11 C12 C13 121.25(19) . . ?
 C13 C12 H4 119.4 . . ?
 C4 C13 C12 120.65(19) . . ?
 C4 C13 C14 120.69(18) . . ?
 C14 C13 C12 118.67(18) . . ?
 C13 C14 H9 119.5 . . ?
 C15 C14 C13 121.10(19) . . ?
 C15 C14 H9 119.5 . . ?
 C14 C15 H8 120.0 . . ?
 C14 C15 C16 120.1(2) . . ?
 C16 C15 H8 120.0 . . ?
 C5 C16 C15 120.56(18) . . ?
 C17 C16 C5 119.87(18) . . ?
 C17 C16 C15 119.45(19) . . ?
 C8 C17 C16 121.36(19) . . ?
 C8 C17 H6 119.3 . . ?
 C16 C17 H6 119.3 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N1 C1 C9 C10 -3.2(4) . . . . ?
 N1 C2 C3 C4 176.35(19) . . . . ?
 N1 C2 C3 C10 -7.2(3) . . . . ?
 N1 C2 C11 C12 175.4(2) . . . . ?
 C1 N1 C2 C3 2.0(3) . . . . ?
 C1 N1 C2 C11 -175.63(19) . . . . ?
 C1 C9 C10 C3 -2.7(3) . . . . ?
 C2 N1 C1 C9 3.5(4) . . . . ?
 C2 C3 C4 C5 -167.03(18) . . . . ?
 C2 C3 C4 C13 11.7(3) . . . . ?
 C2 C3 C10 C9 7.3(3) . . . . ?
 C2 C11 C12 C13 5.0(3) . . . . ?
 C3 C2 C11 C12 -2.3(3) . . . . ?
 C3 C4 C5 C6 15.5(3) . . . . ?
 C3 C4 C5 C16 -170.07(17) . . . . ?
 C3 C4 C13 C12 -9.3(3) . . . . ?
 C3 C4 C13 C14 170.65(18) . . . . ?
 C4 C3 C10 C9 -176.5(2) . . . . ?
 C4 C5 C6 C7 178.80(17) . . . . ?
 C4 C5 C16 C15 -4.0(3) . . . . ?
 C4 C5 C16 C17 179.91(16) . . . . ?
 C4 C13 C14 C15 2.3(3) . . . . ?
 C5 C4 C13 C12 169.53(17) . . . . ?
 C5 C4 C13 C14 -10.5(3) . . . . ?
 C5 C6 C7 C8 -0.5(3) . . . . ?
 C5 C16 C17 C8 2.6(3) . . . . ?
 C6 C5 C16 C15 170.82(17) . . . . ?
 C6 C5 C16 C17 -5.3(3) . . . . ?
 C6 C7 C8 C17 -2.4(3) . . . . ?
 C7 C8 C17 C16 1.3(3) . . . . ?
 C10 C3 C4 C5 17.0(3) . . . . ?
 C10 C3 C4 C13 -164.30(19) . . . . ?
 C11 C2 C3 C4 -6.1(3) . . . . ?
 C11 C2 C3 C10 170.30(18) . . . . ?
 C11 C12 C13 C4 1.1(3) . . . . ?
 C11 C12 C13 C14 -178.9(2) . . . . ?
 C12 C13 C14 C15 -177.7(2) . . . . ?
 C13 C4 C5 C6 -163.22(18) . . . . ?
 C13 C4 C5 C16 11.2(2) . . . . ?
 C13 C14 C15 C16 5.3(3) . . . . ?
 C14 C15 C16 C5 -4.3(3) . . . . ?
 C14 C15 C16 C17 171.78(19) . . . . ?
 C15 C16 C17 C8 -173.51(19) . . . . ?
 C16 C5 C6 C7 4.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
